After dinner, we went "parking" in a lot by a nearby playground. Jenny's body felt great in my hands, and I brought her to orgasm with my fingers several times. Once again my cock strained at its cage, craving release. I figured I already knew what the answer would be, but my desperate cock wouldn't allow me to not even ask.

"Jenny," I asked during a lull in the making out, "do you think I could maybe cum tonight?"

She actually seemed to consider it for a moment, then she shook her head with a smile. "No, I don't think so," she said simply. This was the major question in my life at the moment, and she had ruled on it as casually as if I'd asked her if she wanted some ice cream. I was both thrilled and appalled at this new power dynamic in our relationship.

We went home but she wasn't done with me yet. She told me to wait on the sofa while she changed. She came back out in the blue teddy, dangling the handcuffs from her hand. "Turn around," she said.

Shortly we were making out again, me with my hands cuffed behind my back and my pants and chastity belt laying on the floor. She would massage my cock and balls for a while, then call a "break" and let me cool down and relax a bit. After two of these cycles, I found myself having to control my breathing. After five, I was going batty. In some ways, this was the most maddening teasing yet; something about her ramping me up then letting me cool down again was more frustrating than just a sustained tease.

It didn't help that I was fighting her. I'd try to think about something else, anything else, to keep from getting hard. But it never took her more than a few seconds to get me completely hard again. And I may have made things tougher for myself. Once, as I felt my cock stiffen, I whispered "Damn" to myself, but loud enough for her to hear. Her eyes widened, then she smiled. I'm pretty sure she figured out I was fighting her, and that she gave me a couple extra cycles as "victory laps."

During one of the breaks, I decided to make one last attempt to cum that day. I knew it was probably futile, but again the pressure coming from my cock was incredible.

She took my cock in her hand again. It stiffened at her mere touch. "Oh? Anything?"

I nodded. She began teasing my cock in earnest. "Would you pay money to cum?"

"Yes! Yes, of course," I said.

"Would you give me all the money in your wallet?" she asked.

I nodded. "Oh, yes." I felt like I was on the verge, that I might finally get to cum.

She stopped her teasing for a moment while she reached down and fished my wallet out of my pants. She opened it up and took out all the cash, three twenties.

"Sixty bucks?" she scoffed. "All the time, effort and money I've put in the last few days and you want me to end it all for sixty bucks?" She tossed the wallet and cash on the floor and went back to teasing my desperate cock.

"Of course, you could always write me a check," she said.

"Sure. Okay." I was practically shivering with frustration at this point.

"How about a hundred dollars?" she asked.

I nodded enthusiastically. "Okay."

She seemed to consider it. "How about two hundred dollars?" I only hesitated a second before nodding. Her fingers on my cock put me in a very weak negotiating position.

"Hmmm. I think three hundred would be reasonable. Don't you?" The Hell of it is, I did. Three-hundred dollars was a good chunk of my weekly pay in those days, and parting with it would mean cutting back on a lot of things in the next two or three weeks. But in that moment, it seemed like the most reasonable offer in the world.

"Really?" she asked. "You'd pay me $300 for a thirty-second handjob with a happy ending?"

I nodded again. "I'd pay you $300 to let me do it myself."

She laughed. "That's fantastic." She stopped teasing me, got up, and got my belt. She sat with it on her lap. "I'm afraid I must decline your generous offer."

I was devastated.

"I'm just not ready for you to cum yet," she continued. "And besides, I have a couple of new skirts I want to try out this week." I groaned. "New skirts" meant work clothes, and this was only Saturday night. It would be at least three more days in the belt.

Speaking of the belt, she soon got me back in it. I cooperated as best I could, as much from not wanting to repeat my pathetic performance earlier as from wanting to avoid having my time extended. After she let me out of the cuffs, she went and got us glasses of wine. I slumped on the couch, staring glumly at my belt.

"Oh now, don't be that way," she said. "It's not that bad."

I smirked. "We’ll see what you say after I've had you in one of these for a couple of weeks," I said.

She laughed. "I don't think so. Remember? Chastity is for you, not for me." She took a sip of wine. "In fact, not too long after we finish this stretch, I think we need to try one a bit longer. Say, a month?"

I could have protested it was unfair. I could have said I wouldn't do it. But I knew I would. Because as frustrating as I found this whole experience, it was also turning me on more intensely than anything ever had before. Somehow, Jenny had brought something out in me. Had it been there all the time, waiting to be set free? Or had she imprinted me with it to service her own kink? Either way, I craved being tormented as much as she enjoyed tormenting. A month? The idea was horrifying, but also thrilling as Hell.

It was getting late so we went to bed. Jenny fell right asleep. And why not? She'd had several orgasms, two good meals, and lots of good heavy petting that day. Me? I'd been ruthlessly teased pretty much the whole day, nearly had a nervous breakdown, and had yet another record-breaking case of blue balls. So it took me a little longer.

The next morning, Sunday, I was up before Jenny. I was in the kitchen making coffee when she came in, completely naked.

"Come on, I have something for you," she said leading me back into the bedroom. She unlocked my belt and threw it on the floor. Then she made me sit down on the edge of the bed and she got down on her knees in front of me.

"Same rules," she said. "If you touch me or your penis before I say so, I'm putting you back in the belt so long you'll forget what an orgasm feels like. Got it?"

I said I did. I leaned back on my arms as she gave me a slow blow job. After only a minute I wanted to cum again. After five minutes I was desperate to cum again. I grunted and moaned in frustration, causing her to giggle as her tongue tortured my cock.

Then she stopped. Still kneeling in front of me, she picked up the cutoff jeans she'd been wearing yesterday while "we" cleaned, and before that on Friday night when she'd tried to get me to touch my cock. She took a piece of paper out of a pocket; it was the one where she'd re-figured the time on my "extension." She held it up so I could read it. There were a lot of numbers scrawled on it, then along one edge she'd written "Sunday 11:00 am" and circled it. She pointed to the clock. it was 11:00 am.

"Time for you to cum," she said brightly, then she leaned forward and took my cock nice and deep into her mouth. Her tongue, an instrument of torture only a minute before, sent wave after wave of pleasure through me. I felt an orgasm start to build right away. For a second I was afraid this was just another tease, but she brought me closer and closer.

When it happened, it was the most incredible thing I've ever felt.

*****

Things went back to normal for awhile. I think Jenny realized I needed a break, and she probably needed one, too. It occurred to me she must have been planning and saving for the “long game” for quite awhile before we got started. That and the effort of being such a creative and persistent cock tease had to be a lot of work, however much she enjoyed it.

Occasional chastity play was still part of our sex life. One time she locked me in the belt in the morning and said it was "just for a day or two." I was pretty nervous, afraid this was going to turn into that month-long "stretch" she had mentioned so casually. She got me good and teased up and the following morning, about five minutes before I usually left for work, she made me an offer: I could get out of the belt and cum now, or I would have to wait until the next morning at the same time. The catch was, I would be late for work, which I hated. She said the offer was only valid at that time every morning on weekdays. I wanted to cum right then, but my ego wouldn't let me cave right away, plus I knew she liked it when I resisted her (as long as she won eventually, of course), so I managed to hold off for a couple days. At that point, it was Friday morning, so the choice was either give in or spend the weekend frustrated in the belt, so I gave in. My dick always won out over my ego eventually.

But life got in the way. Not long after that, Jenny got a promotion at work, which soon led to her spending long periods away from home. At one point early on, she put me in the belt then left town for four days. It was hot in its own way, but not nearly as intense as when we were together. Things kind of petered out after that. Eventually, Jenny was permanently transferred and we broke up. Things had cooled to the point where we never even talked about me moving with her.

I never spent that month in chastity, at least with Jenny. I have spent longer periods in chastity with subsequent partners, and they were no picnic, but they haven't messed with my body and my mind as intensely as during those two weeks playing Jenny's "long game." Maybe it's because I was older, maybe it's because I now wanted to be teased and denied, maybe it's because those women weren't as relentless with their teasing as Jenny was. Those women that came later certainly drove me crazy in their own way at times, but with Jenny's "long game" it felt like that all the time.